Thanks for that. Yes, there are definitely some circumstances where thinking in terms of risk is a plus.

As a bit of a dovetail, I had another random thought after typing the previous message. Technical debt is a little bit different than monetary debt because if I borrow money to leverage the business, the business (hopefully) grows in the same currency that I borrowed. I make more money and can pay it back.

Technical debt is different because even if I make a lot of money by taking a technical short cut, it doesn't mean I will have the capability of repaying the "loan". The people who made that short cut may not be capable of refactoring the code. Hiring people who can do the work seems like it would help, but then you have all the problems discussed in the original article.

Looking at it from the risk perspective, it can be a lot clearer that you might want to avoid the situation right from the off. Although the person who prompted me to write my response has unfortunately been entirely unhelpful, I suspect that's what they were ultimately thinking. "Will you actually be able to pay off this technical debt even if you grow the business?" Sometimes you can look at your staff and say that the risk of failure is nearly 100% ;-)